59. The preparation of diazomethane and its homologues

Adamson, D. W.; Kenner, J.

doi:10.1039/jr9350000286

Cited by 39 publications

(7 citation statements)

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“…This quartz reactor should be filled initially with liquid Nitrogen, which will become the reaction medium. We suggest that for the synthesis of methylene we use nitrosomethyl-urea (G1) (Arndt & Amende 1930;Adamson & Kenner 1935;Arndt 1943). For generating nitrene one can use sodium or potassium azides (G2) (Miller et al 1946;Brase & Banert 2010).…”

Section: Methodsmentioning

confidence: 99%

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Syntone chemistry and prebiotic stage in life evolution 1. Aziridinone, a key compound in formation of the first proteinogenic amino acids and polypeptides

Surpateanu

2017

International Journal of Astrobiology

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In this paper is proposed a new theory concerning the formation of the first proteinogenic amino acids and their corresponding polypeptides starting of three syntones: methylene, nitrene and carbon monoxide. First, at low temperature in nitrogen, these three syntones form aziridinone, an asimetric compound in special conditions. Next, by a series of radical chain, izomerization, cyclization, elimination and polymerization reactions, apparently without a well defined transition states are formed a series of precursor syntones. Finally, these more structured syntones at the contract with the components of primary atmosphere, especially with water, ammonia, hydrogen sulphide, even with carbon dioxide and methane offer the first proteinogenic amino acids and their first corresponding polypeptides. As a very important aspect, the aziridinone cycle furnish the backbone of proteinogenic amino acids. The formation of each proteinogenic amino acid moiety also as its participation to construction of polypeptide structures were estimated by two parameters: (1) the complex structural factor, Fe and (2) the participation coefficient, Cp respectively. Dominantly, the quantitative results given in this paper were acquired by structural, thermodynamical and reactivity studies using DGauss with the B88-LYP GGA energy functional with high integral accuracy. Finally, an experimental assembly for obtention of amino acids and polypeptides is proposed. Brief, the three initial syntones: CH2, NH and CO, in nitrogen form aziridinone. That, in reactions with the same three syntones form, the more structured syntone precursors of proteinogenic amino acids and polypeptides. At the contact with primary atmosphere components are formed the first proteinogenic amino acids and polypeptides. The first polypeptides appear from polypeptide precursors and not from proteinogenic amino acids.

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Section: Methodsmentioning

confidence: 99%

“…We suggest that for the synthesis of methylene we use nitrosomethyl-urea (G1) (Arndt & Amende 1930; Adamson & Kenner 1935; Arndt 1943). For generating nitrene one can use sodium or potassium azides (G2) (Miller et al .…”

Section: Methodsmentioning

confidence: 99%

Syntone chemistry and prebiotic stage in life evolution 1. Aziridinone, a key compound in formation of the first proteinogenic amino acids and polypeptides

Surpateanu

2017

International Journal of Astrobiology

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“…Intramolecular 1,1-cycloaddition of 163 Although the first report of the preparation of vinyldiazomethane (177) appeared some 70 years ago,70 it took an additional 25 years for the appearance of a report on its cyclization to pyrazole (179). 71,72 Additional examples are discussed in the text.…”

Section: 7-electrocyclizations and Miscellaneousmentioning

confidence: 99%

1,5-Dipolar cyclizations

Taylor¹,

Turchi²

1979

Chem. Rev.

205

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“…(5) From N-nitroso-$-ethylaminoisobutyl methyl ketone. This reagent was prepared in 60-67% yields from mesityl oxide and 33% aqueous ethylamine essentially as described previously (8,16), and observing the necessary precautions during distillation, 100-103°( 1 mm.). Several different reagents were tried for the decomposition to diazoethane, including sodium in isopropyl alochol, potassium hydroxide in n-propyl or isopropyl alcohol, and sodium in cyclohexanol.…”

Section: Preparation Of Diazohydrocarbonsmentioning

confidence: 99%

The Use of Higher Diazohydrocarbons in the Arndt-Eistert Synthesis

Wilds¹,

Meader²

1948

J. Org. Chem.

138

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procedure, are summarized in Table X. There is some indication that the n-propylamine used to prepare the 1-diazopropane was not entirely pure, which may account in part for the lower yields and less pure products in this series. SUMMARY 1. Procedures have been developed which make it possible to use the Amdt-Eistert reaction with higher diazohydrocarbons.2. The reaction has been employed with diazoethane and 1-diazopropane to prepare -methyl and -ethyl homologs, respectively, of the starting acid.3. An improved method for effecting rearrangement of the diazoketones was developed, involving heating at 180-190°with benzyl alcohol and a tertiary amine.Madison 6, Wis.

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59. The preparation of diazomethane and its homologues

Cited by 39 publications

References 0 publications

Syntone chemistry and prebiotic stage in life evolution 1. Aziridinone, a key compound in formation of the first proteinogenic amino acids and polypeptides

Syntone chemistry and prebiotic stage in life evolution 1. Aziridinone, a key compound in formation of the first proteinogenic amino acids and polypeptides

1,5-Dipolar cyclizations

The Use of Higher Diazohydrocarbons in the Arndt-Eistert Synthesis

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